Estate Chocolate Hole and Great Cruz Bay holiday rentals

We found 3,462 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Estate Chocolate Hole and Great Cruz Bay by choosing from 56 houses, 84 flats and other holiday rentals. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Estate Chocolate Hole and Great Cruz Bay

Showing deals for:13 Nov - 20 Nov

Living area
Living area
Exterior
Interior
Exceptional
(41 reviews)

Blue Serenity - Luxury, Oceanfront, Private Beach Access and Pool

St. Thomas

8% off
S$16,831
for 7 nights, 1 villa
S$2,404 per night
includes taxes & fees
Blue Serenity - Luxury, Oceanfront, Private Beach Access and Pool
Main level dining
Outdoor entertainment area
Main level living room
Property grounds
Exceptional
(43 reviews)

Minutes from Magens Bay, gated property, large pool & outdoor entertainment area

St. Thomas

7% off
S$5,621
for 7 nights, 1 home
S$803 per night
includes taxes & fees
Minutes from Magens Bay, gated property, large pool & outdoor entertainment area
Gate from the large upper driveway to the lower driveway and house entry
Steps to secluded each with good snorkeling in all directions.
The house has various options of shaded decks overlooking the water.
Spacious Kitchen
Exceptional
(46 reviews)

Spectacular beachfront villa. Great SNORKELING, kayaking, sunrise & sunset views

St. John

8% off
S$7,216
for 7 nights, 1 villa
S$1,031 per night
includes taxes & fees
Spectacular beachfront villa. Great SNORKELING, kayaking, sunrise & sunset views
View of Caribbean Sea from the comfort of your bed. ☺️
Incredible view of Caribbean Sea.
Pathway to the airstream 😎
Exterior
Exceptional
(33 reviews)

Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

St. Thomas

9% off
S$1,151
for 7 nights, 1 home
S$164 per night
includes taxes & fees
Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets
Private kitchen
Deck at night
Room
Dining table
Exceptional
(70 reviews)

3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor

St. Thomas

8% off
S$6,416
for 7 nights, 1 home
S$917 per night
includes taxes & fees
3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor
Kitchen
Ahhh...
Pool side dining
Abi Beach below-beach bar and restaurant
Exceptional
(152 reviews)

Private Paradise! One level, panoramic views from every room!

St. Thomas

8% off
S$8,782
for 7 nights, 1 villa
S$1,255 per night
includes taxes & fees
Private Paradise! One level, panoramic views from every room!
First bedroom has a  king sized bed, ac, flat screen tv, bathroom
The view looking out from living room
Private kitchen
Terrace level pool (one of 3 on the property including the ocean level pool)
Exceptional
(166 reviews)

Stunning Ocean Views! Walk To Beaches/Beach Bars/Restaurants

St. Thomas

7% off
S$3,683
for 7 nights, 1 villa
S$526 per night
includes taxes & fees
Stunning Ocean Views! Walk To Beaches/Beach Bars/Restaurants
Room
Down Island View!
Kitchen/Dining
Bathroom
Exceptional
(9 reviews)

Remodeled Corner Unit D211 with washer & dryer. Sleeps 4

St. Thomas

7% off
S$4,973
for 7 nights, 1 apartment
S$710 per night
includes taxes & fees
Remodeled Corner Unit D211 with washer & dryer. Sleeps 4
Dining
Pool
Outdoor dining
Interior
Exceptional
(96 reviews)

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

St. Thomas

7% off
S$4,003
for 7 nights, 1 apartment
S$572 per night
includes taxes & fees
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
Property grounds
Property grounds
Villa from the pond in kayak
Private kitchen
Exceptional
(18 reviews)

"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.

St. John

9% off
S$3,750
for 7 nights, 1 villa
S$536 per night
includes taxes & fees
"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.
The patio and beach right in front of you!
Pool
Socially distancing beach bar area for taking a drink or lunch to the beach
The Beach Bar with live music and grill on the property
Exceptional
(65 reviews)

Beach, Bed and Beyond! WiFi included , New Tiled Shower!

St. Thomas

8% off
S$3,669
for 7 nights, 1 apartment
S$524 per night
includes taxes & fees
Beach, Bed and Beyond! WiFi included , New Tiled Shower!
Living area
Exterior
Interior
Terrace/patio
Exceptional
(20 reviews)

Home with panoramic views with access to private beach!

St. Thomas

8% off
S$16,162
for 7 nights, 1 villa
S$2,309 per night
includes taxes & fees
Home with panoramic views with access to private beach!
Living area
Dining
Interior
Pool
Exceptional
(7 reviews)

Oceanfront Sunrise Escape + Backup Power & 3 Pools

St. Thomas

8% off
S$2,259
for 7 nights, 1 apartment
S$323 per night
includes taxes & fees
Oceanfront Sunrise Escape + Backup Power & 3 Pools
Mimosas, anyone?
Welcome to our slice of paradise!
Evening Cocktails......can't beat that view!
Property grounds
Steps, literally steps, to the beautiful waters of the Caribbean
Exceptional
(10 reviews)

Carribean Sea Just Steps from Your Patio!!

St. Thomas

8% off
S$3,792
for 7 nights, 1 apartment
S$542 per night
includes taxes & fees
Carribean Sea Just Steps from Your Patio!!
King size custom made bed, with storage on all sides
View of the mountains from your bed!
Parking right outside your front door, shaded place to sit and relax.
Private kitchen
Exceptional
(37 reviews)

Island Escape for Two, Class and Comfort

St. John

8% off
S$2,261
for 7 nights, 1 apartment
S$323 per night
includes taxes & fees
Island Escape for Two, Class and Comfort
Bedroom
From the balcony
Hummingbirds flock these flowers
Fully equipped kitchen
Exceptional
(41 reviews)

Affordable, oceanfront and walk to private beach gem

St. Thomas

7% off
S$3,508
for 7 nights, 1 apartment
S$501 per night
includes taxes & fees
Affordable, oceanfront and walk to private beach gem
Dining
Property grounds
Private kitchen
Interior
Exceptional
(9 reviews)

Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!

St. Thomas

7% off
S$2,679
for 7 nights, 1 apartment
S$383 per night
includes taxes & fees
Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
Living area
Property grounds
Room
Private kitchen
Exceptional
(12 reviews)

Beautiful Villa on Point Pleasant Resort

St. Thomas

8% off
S$7,162
for 7 nights, 1 villa
S$1,023 per night
includes taxes & fees
Beautiful Villa on Point Pleasant Resort
This IS the view from our patio! 37 steps to the water!  It has been remodeled.
Another view of the pool area.
View of condo from front door entrance.
Resort.  Our condo is right at the tip of the arrow.
Exceptional
(215 reviews)

Oceanfront Ground Floor Condo. 37 Steps to the Water

St. Thomas

8% off
S$3,473
for 7 nights, 1 apartment
S$496 per night
includes taxes & fees
Oceanfront Ground Floor Condo. 37 Steps to the Water
Room
Areal view og Cowpet Bat West.
Living area
Relax reading a book on the bench with 
ocean splashing in the background.
Exceptional
(82 reviews)

BELLA VISTA Villa - Cowpet Bay West; Beach, Pool, Restaurants, Views, & Breezes

St. Thomas

7% off
S$5,245
for 7 nights, 1 apartment
S$749 per night
includes taxes & fees
BELLA VISTA Villa - Cowpet Bay West; Beach, Pool, Restaurants, Views, & Breezes
Room
Our Actual Balcony and View of the Amazing Sapphire Beach Marina!
A casually elegant space to enjoy your time at the beach! Photos from Sept 2022!
Apple TV, Netflix App, DVD/BlueRay with movies & 50MB Fiber Internet!
Exceptional
(134 reviews)

5★ Sapphire Dream! Ocean & Marina Views-Sapphire Beach Condo-Luxury Reno!

St. Thomas

7% off
S$3,854
for 7 nights, 1 apartment
S$551 per night
includes taxes & fees
5★ Sapphire Dream! Ocean & Marina Views-Sapphire Beach Condo-Luxury Reno!
Gorgeous outdoor deck on the sand!
The Pool
Exterior
Bedroom
Exceptional
(13 reviews)

Sapphire Beach Resort Rental

St. Thomas

20% off
S$5,330
for 7 nights, 1 apartment
S$761 per night
includes taxes & fees
Sapphire Beach Resort Rental
Living area with 49” SONY SmartTV and great WIFI for all your Netflix, Hulu, etc
The tranquil sound of the waves is ever present.  You just can’t beat the view.
Master bedroom
Fully equipped kitchen with brand new fridge, microwave, and all cookware
Exceptional
(25 reviews)

FABULOUS! So close you can taste the ocean - Amazing NEWLY RENOVATED condo !

St. Thomas

7% off
S$2,298
for 7 nights, 1 apartment
S$328 per night
includes taxes & fees
FABULOUS! So close you can taste the ocean - Amazing NEWLY RENOVATED condo !
Private kitchen
Interior
Aerial view
Interior
Excellent
(20 reviews)

Cozy stay, next to lookout and 10 minutes for Magens Bay Beach

St. Thomas

5% off
S$1,747
for 7 nights, 1 villa
S$250 per night
includes taxes & fees
Cozy stay, next to lookout and 10 minutes for Magens Bay Beach
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Estate Chocolate Hole and Great Cruz Bay getaway

Learn about the unique charm of Estate Chocolate Hole and Great Cruz Bay with a stay in a holiday home rental. This city has something for everyone. Trunk Bay and Virgin Islands National Park are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Estate Chocolate Hole and Great Cruz Bay

Are you hoping to find attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Estate Chocolate Hole and Great Cruz Bay a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Mahogany Run Golf Course (8.4 mi / 13.5 km)
  • The Self Centre (2.1 mi / 3.4 km)

Exploring the natural features in Estate Chocolate Hole and Great Cruz Bay

Whether you're an adventurous traveller or just want to appreciate the scenery, Estate Chocolate Hole and Great Cruz Bay is a great place to get out in nature. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Trunk Bay (2.5 mi / 4.1 km)
  • Virgin Islands National Park (3 mi / 4.8 km)
  • Sapphire Beach (4.4 mi / 7.1 km)
  • Chocolate Hole (0.3 mi / 0.5 km)
  • Great Cruz Bay (0.5 mi / 0.7 km)
  • Cruz Bay Beach (1.1 mi / 1.8 km)

Transport to and around Estate Chocolate Hole and Great Cruz Bay

The nearest airport is in St. Thomas (SPB-St. Thomas Seaplane Base), located 10.4 mi (16.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into St. Thomas (STT-Cyril E. King), which is 12.4 mi (19.9 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Estate Chocolate Hole and Great Cruz Bay?
The most in-demand types of holiday rentals in Estate Chocolate Hole and Great Cruz Bay are villas. Hoping for something different? Vrbo has many options to match the unique needs of our guests, so you'll see holiday homes in all sizes and shapes. The perfect fit is ready and waiting for you — discover yours today.
How much does it cost to rent a holiday rental in Estate Chocolate Hole and Great Cruz Bay?
The average price for a holiday rental in Estate Chocolate Hole and Great Cruz Bay is determined by several factors, such as property type, length of stay and season. Whether you're in search of a sprawling villa with space for extended family or a cosy cabin ideal for just you and the kids, just add your travel dates to find stays with exceptional value.
How much does it cost to rent a beach house in Estate Chocolate Hole and Great Cruz Bay?
Prices for beach houses in Estate Chocolate Hole and Great Cruz Bay can differ depending on the size and style of the property and when you're travelling. Simply enter your dates of travel into Vrbo and the number of guests to view your rental options and prices. From there you can use our filters to narrow your search results by ratings, amenities, nearby activities and more.
Are there pet-friendly holiday rentals in Estate Chocolate Hole and Great Cruz Bay?
Yes, there are. You can choose from 310 holiday rentals that allow pets in Estate Chocolate Hole and Great Cruz Bay. Several of our pet-friendly holiday rentals even have an outdoor space for your furry friend to play around in, complimentary treats, special dog beds and proximity to parks. Apply the "Pets allowed" filter to find your place on Vrbo.
Can I rent a house with a pool in Estate Chocolate Hole and Great Cruz Bay?
Add an extra layer of fun to your holiday by booking one of the 270 houses with a private pool in Estate Chocolate Hole and Great Cruz Bay. Use our search filter to find properties with pools on Vrbo, then spend leisurely days splashing and playing in a swimming pool that's all yours.
What are popular rental amenities in Estate Chocolate Hole and Great Cruz Bay?
A fireplace, a swimming pool and ski-in/ski-out facilities head the list of most popular rental amenities in Estate Chocolate Hole and Great Cruz Bay. Whether you're heading away solo, with your sweetheart or a group of dear friends, Vrbo can help you find a holiday rental that matches your style with all the options you need.
Are there large group holiday rentals in Estate Chocolate Hole and Great Cruz Bay?
Estate Chocolate Hole and Great Cruz Bay has 58 holiday homes that can fit 10 or more guests. These stays come with plenty of space to share good times with family and friends.
Are there holiday rentals in Estate Chocolate Hole and Great Cruz Bay that welcome kids?
Estate Chocolate Hole and Great Cruz Bay has 307 family-friendly holiday homes to pick from. And finding a stay that welcomes kids is a cinch with Vrbo's "Properties good for families" filter. Besides having the whole place to yourselves, you'll enjoy access to conveniences and perks like extra bedrooms, full kitchens and private pools.
What are the top attractions for families in Estate Chocolate Hole and Great Cruz Bay?
Keep the kids amused at these fun family-friendly attractions in Estate Chocolate Hole and Great Cruz Bay:
  • Trunk Bay
  • Cruz Bay Beach
  • Honeymoon Beach
Are there one-bedroom holiday rentals in Estate Chocolate Hole and Great Cruz Bay?
You can pick from 42 one-bedroom rentals in Estate Chocolate Hole and Great Cruz Bay. Whether you're on the lookout for a cosy cottage or a condo, Vrbo's one-bedroom properties are perfect if you don't need huge amounts of space. One of the best things about having your own pad? You won't ever need to share your adventure with strangers.
Can I find two-bedroom holiday rentals in Estate Chocolate Hole and Great Cruz Bay?
Estate Chocolate Hole and Great Cruz Bay has 124 two-bedroom holiday properties for you to pick from. Book a holiday home with all the privacy and comfort you're looking for at a price that won't break the bank on Vrbo.
Are there holiday rentals with WiFi in Estate Chocolate Hole and Great Cruz Bay?
Take your pick of 60 holiday rentals with WiFi in Estate Chocolate Hole and Great Cruz Bay. If you want to disconnect from the world on your escape, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Estate Chocolate Hole and Great Cruz Bay?
Estate Chocolate Hole and Great Cruz Bay has 294 holiday rentals where you can relax and recharge in air-conditioned comfort. To book a stay on Vrbo that features this amenity, choose your travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Estate Chocolate Hole and Great Cruz Bay?
The minimum age is generally 16, 18 or 21. It can differ across properties on Vrbo, so look at the rules of your chosen Estate Chocolate Hole and Great Cruz Bay stay before booking.
How long can I rent a holiday rental in Estate Chocolate Hole and Great Cruz Bay for?
The amount of time you can book an Estate Chocolate Hole and Great Cruz Bay holiday home for depends on each property. Simply tap in your travel dates to see options that offer long-term stays. They have all you need to make your extended getaway more comfortable and convenient, like air conditioning and kitchens. Some properties may also offer discounted weekly or monthly prices, so you can stay longer for less money.

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